Taking a Learning Break/Upskilling to get the role you want - How to think about it?

Question

I’ve seen questions recently about people wondering whether to pursue an MBA of a CS Masters which comes at the expense of either maintaining your current tech job or searching for a new one. My question is slightly different: When is it worth taking a learning sabbatical if ever?

By learning sabbatical, I mean I have seen people put on LinkedIn that they did quit their jobs to do a bootcamp in some field (Mobile, Blockchain, etc) or even just self-study on their own. I have a coworker who’s a business analyst and told me he’s quitting to do a data science bootcamp. Doesn’t seem like a good idea to me, but not my decision.

I think the general rule people follow is to have a job while looking for one, particularly in this economy. Still, I’m wondering about what circumstances actually warrant quitting a job to invest in getting one in a different field. Obviously being in a toxic environment is the best reason to get out of a current job. Similarly, if you really need the money, you probably can’t leave the job.

So let’s assume that neither is the case. You don’t need the money and the environment is positive, but you’re really not doing what you’re passionate about and feel like every day you are missing learning cool stuff. Say you’re a business analyst and want to become a data scientist or backend software engineer. An obvious move is to try and switch into these roles within your current company. But if you can’t do that, how to think about taking a learning break?

Casey Dai · Accepted Answer

It comes down to weighing the tradeoffs and not letting "false narratives/stigma" plague your decision.

You've covered the main aspects to consider, which are financial security (and VISA issues, which I assume don't apply here). Here are a few more that I would spend thinking about:

Reentry risk: are you well-established in terms of work history, marketable skills, and professional network to not face too many issues when you do want to pick up another job? Consider your ability to get referrals/interviews from people who will vouch for you in your existing network, your ability to expand your network as needed, and build in a reasonable amount of lead time to obtain a job based on market conditions at that time, how well you interview, etc.
Gains from time off: it sounds like learning is the primary objective of taking time off, so ask yourself if the tradeoff in career progression, foregone salary, etc. are worth was you can reasonably expect to gain. It largely depends on your current progression and what stage you're at. For example, if you're in your promo year, there's probably a better time assuming you want the promo. Conversely, if you're looking to pivot anyways and the market is currently bad, taking a break can be strategic.
Alternatives: are there other ways to acquire the learning for a lower cost? If you're looking for a break for non-career reasons, that's perfectly ok as well (I find it quite toxic that there are any stigmas around that in general). I don't know anyone whose regretted taking a sabbatical every 8-10 years to "recalibrate" in general. Just be sure that you have thought through what you plan to do and what you can realistically gain from it. It can be pretty scary actually to all of a sudden get ALL of your time back after quitting your job.

Taking a Learning Break/Upskilling to get the role you want - How to think about it?

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